In 1823, the bitterness that led to the Civil War surfaced during a match race between the Northern horse American Eclipse and a Southern colt named Sir Henry.
The grudge match inspired fortunes to be wagered, including that of congressman John Randolph.
Randolph put up $10,000 and his entire wardrobe, which gave a newspaper the observation that he was “betting his shirt” on the race.
Incidentally, the race was won by American Eclipse, and Randolph kept his wardrobe.
That’s how “betting your shirt” evolved to mean to gambling everything you own.